Potassium Carbonate → 6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)-4-(4-methylquinolin-7-yloxy)quinazoline

HRID 1791656Notes

Reaction equation

HRID 1791656 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:30][C:31]1[CH:40]=[C:39]2[C:34]([C:35]([CH3:41])=[CH:36][CH:37]=[N:38]2)=[CH:33][CH:32]=1>CN(C=O)C>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])[N:5]=[CH:4][N:3]=[C:2]2[O:30][C:31]1[CH:40]=[C:39]2[C:34]([C:35]([CH3:41])=[CH:36][CH:37]=[N:38]2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 220306904-chloro-6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazolineHCID 1354918544-Methyl-7-quinolinol

Product 1

HCID 220307956-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)-4-(4-methylquinolin-7-yloxy)quinazolineYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazoline (150 mg, 0.42 mmol), (prepared as described for the starting material in Example 152), potassium carbonate (90 mg, 0.63 mmol) and 7-hydroxy-4-methylquinoline (71 mg, 0.46 mmol), (Chem. Berich. 1967, 100, 2077), in DMF (5.0 ml) was stirred at 100° C. for 2 hours and allowed to cool to ambient temperature. The DMF solvent was removed by evaporation and the residue was taken up in 2N aqueous sodium hydroxide solution. The precipitate was filtered off, dried, taken up in dichloromethane and then filtered through phase separating paper. The solution was then evaporated to dryness. The resulting solid was recrystallised from acetonitrile, filtered and washed with diethyl ether to give 6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)-4(4-methylquinolin-7-yloxy)quinazoline (84 mg, 42%).

Workup

  1. custom(prepared
  2. temperatureto cool to ambient temperature
  3. customThe DMF solvent was removed by evaporation
  4. filtrationThe precipitate was filtered off
  5. customdried
  6. filtrationfiltered through phase
  7. customseparating paper
  8. customThe solution was then evaporated to dryness
  9. customThe resulting solid was recrystallised from acetonitrile
  10. filtrationfiltered
  11. washwashed with diethyl ether

Sources & evidence

ORD record
ord-201b31eda4c34809b27034be8982938b
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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